Literature DB >> 31643051

Click Chemistry Conjugations.

Tak Ian Chio1, Susan L Bane2.   

Abstract

Click chemistry has found wide application in bioconjugation, enabling control over the site of modification in biomolecules. Demonstrations of this chemistry to construct chemically defined antibody-drug conjugates (ADCs) have increased in recent years, following studies that support benefits of homogeneity and site-specificity of drug placement on the antibody. In this chapter, a brief history of early applications of this chemistry in ADCs is presented. Examples of click chemistries that are utilized for ADC synthesis, including those currently undergoing clinical investigations, are enumerated. Protocols for two common conjugation methods based on carbonyl-aminooxy coupling and strain-promoted azide-alkyne cycloaddition are described.

Entities:  

Keywords:  Aldehyde; Antibody–drug conjugates (ADCs); Bioconjugation; Click chemistry; Oxime; Site-specific; Strain-promoted azide–alkyne cycloaddition (SPAAC)

Mesh:

Substances:

Year:  2020        PMID: 31643051      PMCID: PMC7444748          DOI: 10.1007/978-1-4939-9929-3_6

Source DB:  PubMed          Journal:  Methods Mol Biol        ISSN: 1064-3745


  49 in total

1.  Conjugation site modulates the in vivo stability and therapeutic activity of antibody-drug conjugates.

Authors:  Ben-Quan Shen; Keyang Xu; Luna Liu; Helga Raab; Sunil Bhakta; Margaret Kenrick; Kathryn L Parsons-Reponte; Janet Tien; Shang-Fan Yu; Elaine Mai; Dongwei Li; Jay Tibbitts; Jakub Baudys; Ola M Saad; Suzie J Scales; Paul J McDonald; Philip E Hass; Charles Eigenbrot; Trung Nguyen; Willy A Solis; Reina N Fuji; Kelly M Flagella; Darshana Patel; Susan D Spencer; Leslie A Khawli; Allen Ebens; Wai Lee Wong; Richard Vandlen; Surinder Kaur; Mark X Sliwkowski; Richard H Scheller; Paul Polakis; Jagath R Junutula
Journal:  Nat Biotechnol       Date:  2012-01-22       Impact factor: 54.908

2.  Site-Specific Bioconjugation and Multi-Bioorthogonal Labeling via Rapid Formation of a Boron-Nitrogen Heterocycle.

Authors:  Tak Ian Chio; Han Gu; Kamalika Mukherjee; L Nathan Tumey; Susan L Bane
Journal:  Bioconjug Chem       Date:  2019-05-03       Impact factor: 4.774

3.  Site-Specific Tandem Knoevenagel Condensation-Michael Addition To Generate Antibody-Drug Conjugates.

Authors:  Romas A Kudirka; Robyn M Barfield; Jesse M McFarland; Penelope M Drake; Adam Carlson; Stefanie Bañas; Wes Zmolek; Albert W Garofalo; David Rabuka
Journal:  ACS Med Chem Lett       Date:  2016-08-30       Impact factor: 4.345

4.  Site-specific antibody-drug conjugation through an engineered glycotransferase and a chemically reactive sugar.

Authors:  Zhongyu Zhu; Boopathy Ramakrishnan; Jinyu Li; Yanping Wang; Yang Feng; Ponraj Prabakaran; Simona Colantonio; Marzena A Dyba; Pradman K Qasba; Dimiter S Dimitrov
Journal:  MAbs       Date:  2014-10-30       Impact factor: 5.857

5.  Rapid oxime and hydrazone ligations with aromatic aldehydes for biomolecular labeling.

Authors:  Anouk Dirksen; Philip E Dawson
Journal:  Bioconjug Chem       Date:  2008-12       Impact factor: 4.774

6.  Formation of hydrazones and stabilized boron-nitrogen heterocycles in aqueous solution from carbohydrazides and ortho-formylphenylboronic acids.

Authors:  Han Gu; Tak Ian Chio; Zhen Lei; Richard J Staples; Jennifer S Hirschi; Susan Bane
Journal:  Org Biomol Chem       Date:  2017-09-20       Impact factor: 3.876

7.  Hydrazino-Pictet-Spengler ligation as a biocompatible method for the generation of stable protein conjugates.

Authors:  Paresh Agarwal; Romas Kudirka; Aaron E Albers; Robyn M Barfield; Gregory W de Hart; Penelope M Drake; Lesley C Jones; David Rabuka
Journal:  Bioconjug Chem       Date:  2013-06-03       Impact factor: 4.774

8.  Aldehyde tag coupled with HIPS chemistry enables the production of ADCs conjugated site-specifically to different antibody regions with distinct in vivo efficacy and PK outcomes.

Authors:  Penelope M Drake; Aaron E Albers; Jeanne Baker; Stefanie Banas; Robyn M Barfield; Abhijit S Bhat; Gregory W de Hart; Albert W Garofalo; Patrick Holder; Lesley C Jones; Romas Kudirka; Jesse McFarland; Wes Zmolek; David Rabuka
Journal:  Bioconjug Chem       Date:  2014-06-23       Impact factor: 4.774

9.  Boronic acids facilitate rapid oxime condensations at neutral pH.

Authors:  Pascal Schmidt; Cedric Stress; Dennis Gillingham
Journal:  Chem Sci       Date:  2015-04-13       Impact factor: 9.825

10.  Characterization and in vitro data of antibody drug conjugates (ADCs) derived from heterotrifunctional linker designed for the site-specific preparation of dual ADCs.

Authors:  Amit Kumar; Krista Kinneer; Luke Masterson; Ebele Ezeadi; Philip Howard; Herren Wu; Changshou Gao; Nazzareno Dimasi
Journal:  Data Brief       Date:  2018-11-06
View more
  2 in total

1.  Selective Enrichment of Sialylglycopeptides Enabled by Click Chemistry and Dynamic Covalent Exchange.

Authors:  Miyang Li; Junfeng Huang; Min Ma; Xudong Shi; Lingjun Li
Journal:  Anal Chem       Date:  2022-04-25       Impact factor: 8.008

2.  Addition of Lauryldimethylamine N-Oxide (LDAO) to a Copper-Free Click Chemistry Reaction Improves the Conjugation Efficiency of a Cell-Free Generated CRM197 Variant to Clinically Important Streptococcus pneumoniae Serotypes.

Authors:  Leslie Bautista; Lucy Pill-Pepe; Neeraj Kapoor; Scott Snyder; Ellen Chu; Paresh Agarwal; Mohammed Sardar; Shylaja Arulkumar; Aym Berges; Mark Iverson; Christopher Behrens; Olivier Marcq; Jeff Fairman
Journal:  ACS Omega       Date:  2022-09-20
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.